You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:46 UTC
HMDB IDHMDB0000947
Secondary Accession Numbers
  • HMDB00947
Metabolite Identification
Common NameUndecanoic acid
DescriptionUndecanoic acid, also known as N-undecylic acid or N-undecanoate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Undecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Undecanoic acid is a potentially toxic compound.
Structure
Data?1582752166
Synonyms
ValueSource
1-Decanecarboxylic acidChEBI
CH3-[CH2]9-COOHChEBI
Hendecanoic acidChEBI
N-Undecanoic acidChEBI
N-Undecoic acidChEBI
N-Undecylic acidChEBI
UDAChEBI
Undecoic acidChEBI
Undecylic acidChEBI
UndekansaeureChEBI
1-DecanecarboxylateGenerator
HendecanoateGenerator
N-UndecanoateGenerator
N-UndecoateGenerator
N-UndecylateGenerator
UndecoateGenerator
UndecylateGenerator
UndecanoateGenerator
1N-Undecoic acidHMDB
FA(11:0)HMDB
Undecanoic acidMeSH
Chemical FormulaC11H22O2
Average Molecular Weight186.2912
Monoisotopic Molecular Weight186.161979948
IUPAC Nameundecanoic acid
Traditional Nameundecanoic acid
CAS Registry Number112-37-8
SMILES
CCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)
InChI KeyZDPHROOEEOARMN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point28.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 mg/mLNot Available
LogP4.42SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP4.49ALOGPS
logP4.03ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity54.08 m³·mol⁻¹ChemAxon
Polarizability23.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0159-2910000000-722a87fa01fa27b58b07Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0706-9000000000-d7f6a00a2bcfd58539f5Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-2910000000-722a87fa01fa27b58b07Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06r6-9400000000-c452aa611294afd4b227Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9310000000-90668bb3fcf413ecc767Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-4e46062530f2b87127f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-2900000000-1bd11599567676fd18b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0019-3900000000-3ed16e9aae084b8128f7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-70bc980554bccc2d565fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-0900000000-1923c2ee9004b1a4f217Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-0900000000-818107787c04dbc613beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-01t9-9000000000-da3c8186be5724d14262Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-052f-9000000000-4a1e2f342d24eb6ec79eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0090000000-2dadd8baad50427686a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03di-0090000000-2dadd8baad50427686a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-d09512035285f332d56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-fca225c5971e85f0f121Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0900000000-0fabd46bd1eaa73e5af0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0900000000-d09512035285f332d56cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-70bc980554bccc2d565fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-1923c2ee9004b1a4f217Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-f871962b32a5d16913f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01t9-9000000000-f75b1abf45a6ce1d1e16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052f-9000000000-4a1e2f342d24eb6ec79eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0900000000-26f27c3846a00308245bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-fca225c5971e85f0f121Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-0900000000-0fabd46bd1eaa73e5af0Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0706-9000000000-f0f2855ce0a7d3e0e44cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-36794ad067903d2b6624Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-157dc43c0ad4ff0f5509Spectrum
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-e152e90785434b58612cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000700
KNApSAcK IDC00007421
Chemspider ID7888
KEGG Compound IDC17715
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUndecylic_acid
METLIN ID5894
PubChem Compound8180
PDB IDNot Available
ChEBI ID32368
Food Biomarker OntologyNot Available
VMH IDM03117
References
Synthesis ReferenceSchreyer, Gerd; Schwarze, Werner; Weigert, Wolfgang. Carboxylic acids by oxidation of vicinal diols. Ger. Offen. (1972), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Avrahami D, Shai Y: Conjugation of a magainin analogue with lipophilic acids controls hydrophobicity, solution assembly, and cell selectivity. Biochemistry. 2002 Feb 19;41(7):2254-63. [PubMed:11841217 ]
  2. Avrahami D, Shai Y: Bestowing antifungal and antibacterial activities by lipophilic acid conjugation to D,L-amino acid-containing antimicrobial peptides: a plausible mode of action. Biochemistry. 2003 Dec 23;42(50):14946-56. [PubMed:14674771 ]
  3. Mingrone G, Greco AV, Capristo E, Benedetti G, Castagneto M, Gasbarrini G: An improved GLC method for a rapid, simultaneous analysis of both medium chain fatty acids and medium chain triglycerides in plasma. Clin Chim Acta. 1995 Sep 15;240(2):195-207. [PubMed:8548929 ]
  4. Kinkaid AR, Wilton DC: A continuous fluorescence displacement assay for phospholipase A2 using albumin and medium chain phospholipid substrates. Anal Biochem. 1993 Jul;212(1):65-70. [PubMed:8368517 ]
  5. Hamfler HW, Nissen HP, Heinze I, Kreysel HW, Schirren C: [Free fatty acid composition of human semen in different clinical diagnoses]. Andrologia. 1978 Nov-Dec;10(6):498-50. [PubMed:736283 ]
  6. Mosley EE, Wright AL, McGuire MK, McGuire MA: trans Fatty acids in milk produced by women in the United States. Am J Clin Nutr. 2005 Dec;82(6):1292-7. [PubMed:16332663 ]
  7. Hornung B, Amtmann E, Sauer G: Medium chain length fatty acids stimulate triacylglycerol synthesis in tissue culture cells. Biochem Pharmacol. 1992 Jan 22;43(2):175-81. [PubMed:1739406 ]
  8. Dutta-Roy AK, Demarco AC, Raha SK, Shay J, Garvey M, Horrobin DF: Effects of linoleic and gamma-linolenic acids (efamol evening primrose oil) on fatty acid-binding proteins of rat liver. Mol Cell Biochem. 1990 Oct 15-Nov 8;98(1-2):177-82. [PubMed:2176271 ]
  9. (). Clinical Guide to Laboratory Tests, 2nd Ed. Norbert W. Tietz 1990. .

Enzymes

General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro). Functions as GTP-dependent lipoate-activating enzyme that generates the substrate for lipoyltransferase (By similarity).
Gene Name:
ACSM1
Uniprot ID:
Q08AH1
Molecular weight:
65272.74
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ACSM6
Uniprot ID:
Q6P461
Molecular weight:
53584.545
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM2A
Uniprot ID:
Q08AH3
Molecular weight:
64223.7
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro).
Gene Name:
ACSM2B
Uniprot ID:
Q68CK6
Molecular weight:
64270.78
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM3
Uniprot ID:
Q53FZ2
Molecular weight:
66152.235
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM5
Uniprot ID:
Q6NUN0
Molecular weight:
64759.55
General function:
Involved in catalytic activity
Specific function:
Has medium-chain fatty acid:CoA ligase activity with broad substrate specificity (in vitro). Acts on acids from C(4) to C(11) and on the corresponding 3-hydroxy- and 2,3- or 3,4-unsaturated acids (in vitro) (By similarity).
Gene Name:
ACSM4
Uniprot ID:
P0C7M7
Molecular weight:
65702.225